This invention relates to an improvement in the process for the production of a mixture of 80-90% 4-(2-nitrobutyl)morpholine and 3-10% 4,4'-(2-nitro-2-ethyltrimethylene)dimorpholine, hereinafter referred to as P-1487.
More particularly, this invention relates to an improvement in the process for the production of P-1487 from the reactants: 1-nitropropane, morpholine and formaldehyde to produce a non-lachrymatory P-1487 product.
The prior known processes for the production of nitro amines, Senkus, U.S. Pat. Nos. 2,474,791 and 2,447,821 teach the production of nitro amines from the reaction of a nitroalcohol and a cyclic secondary amine (2-nitro-2-methyl-1-propanol and morpholine), or a primary amine in which the N substituents are cyclic groups. A second process taught by Senkus in the above patents is the reaction of formaldehyde with a cyclic secondary amine (or primary amine) which, in turn, is reacted with a nitroparaffin. Senkus does not, however, directly teach the reaction of combining the formaldehyde with the nitroparaffin to produce a nitroalcohol which is subsequently reacted with the amine to produce a nitro amine.
A mixture of 80-90% of 4-(2-nitrobutyl)morpholine and 3-10% of 4,4'-(2-nitro-2-ethyltrimethylene)dimorpholine, hereinafter referred to as P-1487, is a known pesticide available commercially. The utility of the mixture as a pesticide is hampered by the high lachrymatory properties of the mixture that appeared to be inherent in the mixture.
The current industrial method of producing P-1487 is well known in the art. In this current industrial method, formaldehyde is reacted with a nitroparaffin at a temperature of between 60.degree.-70.degree. C then the amine, e.g. morpholine, is added maintaining the temperature between 60.degree.-70.degree. C. The present method produces lachrymatory high nitro amine P-1487 product. The formation of the lachrymators was first thought to be due to the production of nitroolefins, which are severe eye irritants. Additional amine (e.g. morpholine) was added to prevent the formation of the nitroolefins or to react with the lachrymators as they were formed to form non-objectionable products. However, the eye irritation and formation of lachrymators remained.